ISSN:
0009-2940
Keywords:
Aziridines, regioselectivity of ring opening
;
Allylamide-enamide isomerization
;
Benzenesulfonamide, N-(1,3-diphenylallyl)
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The title compound 2 can be ring-opened in three ways by alcoholic sodium alkoxide: nucleophilic substitutive opening in (the benzylic) position 3 [attack (a)] and in position 2 [attack (b)] as well as the novel nucleophilic eliminative opening which is initiated by deprotonation of the benzylic substituent [attack (c)]. The primary cleavage product 5 of attack (c) is an allylic sulfonamide that slowly isomerizes to give the elusive enamide 6, the precursor of the isolated ketone 7. Attack (a) predominates with methoxide and less so with ethoxide. Attack (c) increases with size (and basicity?) of the alkoxide and is the only detected reaction with tert-butoxide.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19891220928
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